Plastic containing cellulose acetate



Patti Sept. 16, 1924 HENRY DREYFUS, OF LONDON, ENGLAND.

ELASTIC CONTAINING CELLULOSE ACETATE.

No Drawing. Original application filed August 5, 1920, Serial No. 401,380. Divided and this application filed March 13, 1923. .Serial No. 624,805.

. ter) having a basis of cellulose acetate, and

is characterized by the employment or application of certain new or improved high-boiling solvents or plasticizing agents in and for such solutions, compositions, preparations or products hereinafter and in the claiming clauses included in the term composition of matter.

in addition to the volatile solvents or diluents, such for instance as acetone, alcoholbenzene mixtures, methyl acetate and so forth, which are generally used in making solutions or other products such as referred to, or in some cases even without such volasolvents or diluents, it is necessary to employ solvents or plastioizing agents of higher boiling points,

These latter play an important part, and have to fulfil numerous requirements for use in the art. Besides having a high boiling point they must be liquids or jellies at ordinary temperature or even when cooled down to low temperature, this latter being especially the case for uses where the solutions, compositions or preparations are exposed to low temperatures in service, as in the case of aircraft dopes, outdoor coatings and so forth. Also the-high boiling solvents must be insoluble or very little soluble in water.

"in the specification of a previous U. S.

' Patent No. 1,353,384 filed 15th April 1919, I

- have described the employment as high boil ing'plasticizing solvents for cellulose acetate of high boiling mixtures of isomeric xylene low-carbon-alkyl sulphonamides, which mixtures are liquid at ordinary temperature, and are such as can be obtained by treating an ordinary commercial xylene containing 0, m and p-xylenes, by the ordinary methj elly at 20C.

tate, of high boiling mixtures containing ortho and para toluene low-carbon-alkyl sulphonamides, which mixtures are liquid at ordinary temperature and are such as can be obtained on treating commercial toluene by the ordinary methods of conversion into the alkyl sulphonamides, for example by vtreating the toluene with chlorosulphonic acid to form the corresponding sulphochlorides, treating the resulting raw mixture with ammonia to convert the sulphochlorides into sulphonamides, and then methylating or ethylating to the monomethyl or monoethyl stage; or by treating the said raw mixture with amines such as methylamine, ethylamine, etc.

The present invention is characterized by the employment as plasticizing agents for the purpose mentioned, of certain high boil ing toluene dialkyl sulfonamide preparations which are liquids at ordinary temperature and form jellies at temperatures considerably below ordinary room temperatures,

(a) Mixtures of oand p-toluene dimethyl sulfonamides; Such mixtures boil'at about 133137C. under 1 min.- pressure, are liquid at ordinary temperature, form slightly turbid jelly at 15 C. and a firm turbid (b) Mixtures of oethyl sulfonamides. Such mixtures boil at about 188189C. under 1 mm. pressure, are liquid at ordinary temperature, formsoft, olear jellies at 15C., and firm clear jellies at 20C.

(0) Mixtures of 0- and p-toluene diethyl sulfonamides: Such mixtures boil at about and p-toluene methyl :55 i It will be understood that in cases where the commercial or impure-hydrocarbonis l36142C under 1 mm., are liquid at ordinary temperature, form soft, clear jelly at 10C. and a firm clear mass at .20C. (d) o-toluene dimethyl sulfonamide. This substance boils at about 148-152 C. under 2 mm., is liquid at ordinary temperature, forms a soft, clear jelly at 10C. and a firm, clear jelly. at 20C.

(6) o-toluene diethyl sulfonamide. This substance boils at about l52155C. under 2 mm., is liquid at ordinary temperature, forms a soft, clear jelly at 5C., and a firm clear jelly at 20C.

It has been found that for some applications these toluenc-di-alkylated sulfonamide derivatives are not so good as the mono-alkylated sulfonamide derivatives of my said U. S. Patents No. 1,353,384: and No. 1,353,-

385, as their cellulose acetate solutions tend to become somewhat turbid when cooled down to or below ordinary temperature.

' lVhere this is not objectionable they may even be used alone, but they may be used together with the mono-alkylated sulfonamide derivatives of my said specifications 1,353,384: and 1,353,385 or my application S. No. 101,380 filed August 5, 19:20 of which the present application is divisional, to obtain solutions which remain clear when cooled down, or together with any other suitable high boiling solvents of cellulose acetate- For preparing the said mixtures of o and p toluene dialkyl sulfonamides, ordinary commercial toluene was used distilling between 95 and 132C, and substantially pure toluene boiling at 110-111C. for the o-toluene dimethyl and o-toluene diethyl: sulfonamide product.

. I do not, however, confine myself to working with these particular'grades of hydrocarbon. 7 For example purer to pure toluene may be used for producing the mixturesof oand p-toluene 'dialkyl sulfonamides.

The procedure followed for preparing the alkyl sullfonamide products of the present invention may be according to the ordinary methods of preparing such alkylated compounds via the's'ulphochlorides, these either being treated with ammonia" and thenalkylated with appropgiate alkyla'ting agent such as dimethyl sulp te or ethyl sulphuric acid salt or chlorethy-l etc., or being-treated direct with amines such as methylamine, ethylamine, etc,

indicated above .as having been used, the treatment was carried out thereon without "separation or purification of the interline d1ate or final products, though ll do not con fine myself in this respect.

In the case of the o-toluene dimethyl and dlethyl sulfonamidcs the mixture of oand p-toluene sulfochlorides resulting from neoaeae indicated for the preparation of the alkyl sulfonamides of the present invention and that anyother methods giving substantially similar products may be employed.

The high. boiling plasticizing solvents of the present invention may be employed in any suitable proportions, such for example as those indicated in my said specification No. 1,353,384.

Similarly to the alkylated sulfonamides specified in myflsaid previous patents, the new solvents of the present invention may be employed with any usual or suitable solvents or liquids of low boiling point; likewise any other usual or suitable substances may be added, such as triphenyl phosphate, t'ricresylphosphate or similarly acting agents, or acid neutralizing aliphatic derivatives of urea which are liquid or have a low melt ing point, such as mono-, dior tri-methyl ureau or mono-, dior tri-ethyl urea and so forth.

Also in making the solutions, compositions, or preparations with the solvents of the present invention any of the high boiling solvents of my application S. No. 101,380 or my application S, No. 624,806 divisional thereof, may be added or any other high boiling solvents or softening or plasticizing substances may be added which are liquid substances, or even solid substances, 'protures of two or more of them, or of any of them with alkyl sulfonamide derivatives of my said previous specifications, and about 12 kilos of tricresyl phosphate or triphenyl phosphate, these substances being mixed together with solvents of low boiling point such as acetone, 'methyl acetate or ethyl acetate mixed with alcohol (four volumes to one volume of alcohol), the mass being Worked in the ordinary way in celluloid apparatus, first in the mixers, then on the rollers and afterwards in the presses, and so on, as generally practised in the celluloid industry. This glves quite a hard, incombustible celluloid-like product.

The quantity of about 25 kilos of the alkyl sulfonamide solvents may be reduced together with that of the triphenylphosphate or tricresylphosphate in order to get a still harder product if desired.

On the other hand, by increasing this quantity of the sulfonamide solvents one gets softer products in proportion as the quantity is increased until a product 1s obtained which is pliable like a fabric.

For example, if one takes to 100 kilos of cellulose acetate about 100 kilos of one of the high boiling plasticizing solvents of the present invention (or of a mixture of two or more of them) then one gets the kind of product which is pliable like a fab- .ric, and if the plasticizing solvent is employed in quantities less than 100 per cent reckoned on the weight of the cellulose acetate, a proportionately stifier product is obtained according as the quantity of the plasticizing solvent is reduced, Whilst if the quantity .of the plasticizing solvent .is increased above 100 per cent calculated on the weight of the cellulose acetate, a still more pliable product is obtained.

As stated in my British patent specification No. 114,304, the higher the viscosity of the cellulose acetate the greater the quantity of the high boiling plasticizing solvent which can be used, and the less the viscosity of the cellulose acetate the-smaller the quantity of the high boiling plasticizing solvent which can be used.

Colouring matters, filling materials and any other usual or suitable materials such as commonl employed in the art may of course be a ded in making solutions, compositions dr other products according to the invention.

This ap lication is a division of my application Serial No. 401,380, filed August 5, 1920.

What I claim and desire to secure by Letters Patent is 1. A composition of matter comprising cellulose acetate and a toluene dialkyl sulfonamide preparation which is liquid at ordinary temperature and forms a jelly at low temperatures.

2. A composition of matter comprising cellulose acetate and a plasticizing agent comprising a toluene dialkyl sulfonamide preparation which sulfonamid preparation is liquid at ordinary room temperature and is a jelly at temperatures somewhat below 0 C. and which is a solvent of cellulose acetate at all temperatures below the boiling point of said sulfonamide preparation.

3. A composition of matter omprising cellulose acetate and a mixture of oand p toluene dialkyl sulfonamides, which mixture is liquid at ordinary temperature and forms a jelly at low temperatures.

4. A composition of matter comprising cellulose acetate and a mixture of oand ptoluene diethyl sulfonamides, which mixture is liquid at ordinary temperature and forms a jelly at low temperatures. j

In testimony whereof I have hereunto subscribed my name.

HENRY DREYFUS. 

